2,6-bis(3-bromopropionamido)anthracene-9,10-dione | 864377-54-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2,6-bis(3-bromopropionamido)anthracene-9,10-dione
• CAS: 864377-54-8
• 化学式: C₂₀H₁₆Br₂N₂O₄
• 分子量: 508.166
• InChiKey: GVHGJBVWFBIAEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  92.34
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-甲氧基丙胺 、 2,6-bis(3-bromopropionamido)anthracene-9,10-dione 以 乙醇 为溶剂， 生成 3-(3-Methoxy-propylamino)-N-{6-[3-(3-methoxy-propylamino)-propionylamino]-9,10-dioxo-9,10-dihydro-anthracen-2-yl}-propionamide
  参考文献：
  名称：

  一系列蒽醌与DNA的结合。

  摘要：

  研究了一系列在其侧链带有一个至四个乙二醇单元的同源2，6-二取代蒽醌穿线嵌入剂的DNA结合特性。结合常数通过表面等离振子共振（SPR）测量。这些化合物以比富含GC的发夹略高的亲和力与富含AT的发夹结合。结合常数随着侧链长度的增加而降低。

  DOI：

  10.1016/j.bmcl.2003.10.054
• 作为产物：
  描述：

  3-溴丙烷酰基溴化物 、 2,6-二氨基蒽醌 生成 2,6-bis(3-bromopropionamido)anthracene-9,10-dione
  参考文献：
  名称：

  Amide bond direction modulates G-quadruplex recognition and telomerase inhibition by 2,6 and 2,7 bis-substituted anthracenedione derivatives

  摘要：

  G-quadruplex structures of DNA represent a potentially useful target for anticancer drugs. Stabilisation of this arrangement at the ends of chromosomes may inhibit the action of telomerase, an enzyme involved in immortalization of cancer cells. Appropriately substituted amido anthracenediones are effective G-quadruplex stabilizers, but no information is available as yet on the possible modulation of G-quadruplex recognition and telomerase inhibition produced by the direction of the amide bond. To understand the basis of amido anthracenedione selectivity, we have synthesized a number of derivatives bearing the -CO-NH- or -NH-CO- group linked to the planar anthraquinone (AQ) moiety at 2,6 and 2,7 positions. The various isomers were tested in terms of telomerase inhibition, determined by the TRAP assay, G-quadruplex stabilisation measured by the increase in melting temperature of the appropriately folded oligonucleotide using FRET, and conformational and G4 binding properties examined by molecular modelling techniques. In all cases, enzymatic inhibition and G-quadruplex stabilization were directly related, which strongly supports the proposed molecular mechanism of telomerase interference. Interestingly, the AQ-NH-CO- arrangement performs invariantly better than the AQ-CO-NH- arrangement, showing a clear preference among isomeric derivatives. Theoretical calculations suggest that the former amide arrangement is co-planar with the aromatic system, whereas the latter is tilted by about 30 degrees when considering the most stable conformation. A more extended planar surface would allow more efficient stacking interactions with the quadruplex structure, hence more effective telomerase inhibition. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.09.040